Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
  • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
  • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C211/51—Phenylenediamines
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds

Definitions

• the subject matter of the present invention is a method for making 2-aminomethyl-1,4-diaminobenzene of formula (I) and its physiologically compatible salts with organic or inorganic salts. It also includes compositions and methods for dyeing keratin fibers containing the 2-aminomethyl-1,4-diaminobenzene or its physiologically compatible salts.
• 2-aminomethyl-1,4-diaminobenzene is known as a starting material for making certain heterocyclic compounds and is described in Liebigs Annals of Chemistry (Annalen der Chemie)1978, pp. 398-404. A method of making this compound is however not described. Also attempts to directly produce this compound from commercially obtained 2-amino-5-nitrobenzonitrile of formula (II) have been unsatisfactory in regard to reaction conditions, yield and product quality.
• n is a number from 0 to 3 and HX represents an inorganic or organic salt, which comprises
• Either inorganic or organic acids can be used as the acid ingredient in the above process according to the invention.
• the following acids are preferred: hydrochloric acid, sulfuric acid, boric acid, citric acid and tartaric acid. Hydrochloric and sulfuric acid are especially preferred.
• the amount of the iodide that will result in a higher reaction rate is considerably more than 10% (molar); 50% (molar) has proven to be suitable throughout.
• the reaction can be performed easily in the usual manner in a normal dipolar aprotic solvent under reflux temperature.
• the dipolar aprotic solvent can be, for example, acetone.
• Dialkyl ethers of ethylene glycols and their homologs, preferably those with boiling points under 200° C., such as ethylene glycol dimethyl ether, are suitable as additional solvents.
• the compound of formula (V) is subsequently reduced in an ideal manner according to the conventional method in an ideal way by catalytic hydrogenation with slightly elevated hydrogen pressure or at slightly elevated temperatures.
• the compound of formula (V) is converted into the 1,4-diamino-2-(N-acylaminomethyl)benzene dihydrochloride of formula (VI).
• the compound of formula (VI) is deacylated with hydrochloric acid and the 2-aminomethyl-1,4-diaminobenzene is precipitated as the trichloride of formula (VII).
• This acid adduct may then be easily converted into the free base form or into other salt adducts of the general formula (I). Understandably also one of the intermediates, for example formula (V), could also be used.
• the compounds of formula (I) are outstanding as oxidation dye-precursor compounds for dyeing keratin fibers.
• the present invention also includes compositions and methods for dyeing keratin fibers, especially wool, silk or hair, particularly human hair, using the compounds of formula (I).
• the compounds of formula (I) are especially suitable for dyeing keratin fibers, in principle it would also be possible to dye other natural or synthetic fibers, especially cotton or nylon 66, with these compounds.
• the compounds of formula (I) can be used both alone and also in combination with-certain known developer substances and/or coupler substances, generally known for dyeing fiber materials in oxidative dye systems.
• N-(3-dimethylaminophenyl)urea 2,6-diaminopyridine, 2-amino-4-[(2-hydroxyethyl)amino]anisole, 2,4-diamino-1-fluoro-5-methylbenzene, 2,4-diamino-1-methoxy-5-methylbenzene, 2,4-diamino-1-ethoxy-5-methyl-benzene, 2,4-diamino-1-(2-hydroxyethoxy)-5-methylbenzene, 2,4-di-[(2-hydroxy-ethyl)amino]-1,5-dimethoxybenzene, 2,3-diamino-6-methoxypyridine, 3-amino-6-methoxy-2-(methylamino)-pyridine, 2,6-diamino-3,5-dimethoxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 1,3-
• the compounds of formula (I) may be considered as the developer substances: para-phenylenediamine, para-aminophenols and 4,5-diaminopyrazoles, or their salts.
• the following compounds are especially suitable as developer compounds: 1,4-diaminobenzene (p-phenylendiamine), 1,4-diamino-2-methylbenzene (p-toluylenediamine), 1,4-diamino-2,6-dimethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,3-dimethylbenzene, 2-chloro-1,4-diaminobenzene, 4-phenylaminoaniline, 4-dimethylaminoaniline, 4-diethylaminoaniline, 4-[di(2-hydroxyethyl)amino]aniline, 4-[(2-methoxyethyl)-amino]-aniline, 4-[(3-hydroxypropyl)amino]aniline, 1,4-diamino-2-(2-hydroxy-ethyl)benzene, 1,4-diamino-2-(1-methyl
• the compounds of formula (I) can also understandably be used in combination with various direct-dyeing anionic, cationic or neutral dye compounds.
• anionic dye direct-dyeing dye compounds for use in the compositions of the invention: 6-hydroxy-5-[(4-sulfophenyl)azo]-2-naphthalene sulfonic acid disodium salt (C.I. 15985; Food Yellow No. 3; FD&C Yellow No. 6), 2,4-dinitro-1-naphthol-7-sulfonic acid disodium salt (C.I.10316; Acid Yellow No. 1; Food Yellow No.
• nonionic direct-dyeing dye compounds have proven to be especially useful in the compositions according to the invention: 1-amino-2-[(2-hydroxyethyl)amino]-5-nitrobenzene (HC Yellow No. 5), 1-(2-hydroxyethoxy)-2-[(2-hydroxyethyl)-amino]-5-nitrobenzene (HC Yellow No. 4), 1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Yellow No.
• R represents hydrogen, methyl, ethyl or hydroxyethyl.
• the present invention also includes ready-to-apply hair dye mixtures for oxidative dyeing of hair, which are each made by mixing an oxidation dye precursor composition with an oxidizing agent immediately prior to application. They are characterized by a content of at least one compound of formula (I) as well as additional oxidation dye precursor compounds and/or direct-dyeing dye compounds as needed.
• the compounds of formula (I) and the oxidation dye precursor compounds are contained in the compositions of the invention in total amounts of about 0.01 to 10 percent by weight respectively, preferably from 0.2 to 6 percent by weight.
• the total concentration of direct-dyeing dye compounds in the compositions according to the invention amounts to about 0.1 to 10 percent by weight respectively, preferably from 0.1 to 5 percent by weight.
• antioxidants perfume oils, complex formers, wetting agents, emulsifiers, penetration agents, buffer systems, preservatives, thickeners, care materials and other cosmetic additives may be present in the dye-carrying or oxidation dye precursor composition according to the invention.
• the form of the oxidation dye precursor composition and also for the ready-to-apply dye mixture can be, for example, a solution, especially an aqueous or aqueous-alcoholic solution.
• a solution especially an aqueous or aqueous-alcoholic solution.
• the particularly preferred form of the composition according to the invention is a cream, a gel or an emulsion. Its composition comprises a mixture of the dye ingredients with the conventional additive ingredients usually used in this type of preparation.
• the conventional additive ingredients for solutions, creams, emulsion or gels are, for example, solvents, such as water, lower aliphatic alcohols, for example ethanol, n-propanol and isopropanol or glycols, such as glycerol and 1,2-propylene glycol; wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active substances, such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkyl sulfonates, alkyl benzene sulfonates, alkyltrimethylammonium salts, alkyl betaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanol amides, fatty acid esters; thickeners, such as higher fatty alcohols, starches or cellulose derivative compounds, petrolatum (Vaseline®), paraffin oils and
• compositions according to the invention are included in respective amounts suitable for their purposes.
• the wetting agents and emulsifiers are contained in the compositions according to the invention in concentrations of about 0.5 to 30 percent by weight, the thickeners in amounts of from about 0.1 to 25 percent by weight and the care materials in a concentration of about 0.1 to 5.0 percent by weight.
• the ready-to-apply hair dye mixture according to the invention is made by a method comprising mixing the oxidation dye precursor composition with a liquid oxidizing agent immediately prior to application.
• the oxidation dye precursor composition and the oxidizing agent are mixed with each other inma weight ratio of from 5:1 to 1:3.
• a weight ratio of 1:1 to 1:2 is especially preferred.
• the pH of the ready-to-apply hair dye mixture according to the invention is adjusted during the mixing of the preferred alkaline oxidation dye precursor composition with the mostly acidic oxidizing agent.
• the resulting pH value of the mixture is determined by the alkali content of the dye-carrying or oxidation dye precursor composition, the acid content of the oxidizing agent and the mixing ratio.
• the pH of the ready-to-apply hair dye composition amounts to about 3 to 11, preferably between 6 and 10.5.
• the pH values of both the oxidation dye precursor composition and the oxidizing agent-containing composition can both be adjusted by adding dilute organic or inorganic acids, such as phosphoric acid, ascorbic acid and lactic acid, or bases, such as monoethanolamine, triethanolamine, 2-amino-2-methyl-1-propanol, ammonia, sodium hydroxide, potassium hydroxide or tris(hydroxy-methyl)aminomethane.
• dilute organic or inorganic acids such as phosphoric acid, ascorbic acid and lactic acid
• bases such as monoethanolamine, triethanolamine, 2-amino-2-methyl-1-propanol, ammonia, sodium hydroxide, potassium hydroxide or tris(hydroxy-methyl)aminomethane.
• an amount of the ready-to-apply hair dye mixture sufficient for dyeing the hair is applied to the hair.
• the hair dye mixture is allowed to act on the hair after application for about 10 to 45 minutes at 15 to 50° C., preferably for 30 minutes at 40° C. It is subsequently rinsed from the hair with water. If necessary the hair is washed with a shampoo after rinsing with water and perhaps with a dilute weak organic acid, for example citric or tartaric acid. Subsequently the hair is dried.
• a dilute weak organic acid for example citric or tartaric acid.
• the pH of the cream is between 10 and 10.5.
• the pH of the cream is 10.2.
• oxidation dye precursor composition 100 grams of the above-described oxidation dye precursor composition is mixed with 100 grams of a 6% by weight aqueous hydrogen peroxide solution.
• the resulting ready-to-apply hair dye mixture is applied to bleached hair in the required amount.
• After an acting time of 30 minutes at 40° C. the hair is washed with a shampoo, rinsed with water and dried.
• the dyed hair color is brown with reddish reflections.
• oxidation dye precursor composition 100 grams of the above-described oxidation dye precursor composition is mixed with 100 grams of a 6% by weight aqueous hydrogen peroxide solution.
• the resulting ready-to-use hair dye mixture is applied to bleached hair in the required amount. After an acting time of 30 minutes at 40° C. the hair is washed with a shampoo, rinsed with water and dried. The dye hair color is red-brown with a high chromaticity and brightness.
• a ready-to-apply cream mixture according to example 3 is applied to the textiles listed in Table VI. After an acting time of 30 minutes at 40° C., the cream mixture is neutralized and rinsed out with water.
• German Patent Application 199 61 229.3 of Dec. 18, 1999 is incorporated here by reference.
• This German Patent Application describes the invention described hereinabove and claimed in the claims appended hereinbelow and provides the basis for a claim of priority for the instant invention under 35 U.S.C. 119.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Animal Behavior & Ethology (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Coloring (AREA)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

Country Status (7)

Cited By (3)

Families Citing this family (4)

Citations (2)

• 1999
  • 1999-12-18 DE DE19961229A patent/DE19961229C1/de not_active Expired - Fee Related
• 2000
  • 2000-07-26 EP EP00115959A patent/EP1110942B1/fr not_active Expired - Lifetime
  • 2000-07-26 AT AT03003356T patent/ATE280751T1/de not_active IP Right Cessation
  • 2000-07-26 ES ES03003356T patent/ES2231739T3/es not_active Expired - Lifetime
  • 2000-07-26 DE DE50003892T patent/DE50003892D1/de not_active Expired - Fee Related
  • 2000-07-26 EP EP03003356A patent/EP1310479B1/fr not_active Expired - Lifetime
  • 2000-07-26 ES ES00115959T patent/ES2206115T3/es not_active Expired - Lifetime
  • 2000-07-26 AT AT00115959T patent/ATE251113T1/de not_active IP Right Cessation
  • 2000-07-26 DE DE50008450T patent/DE50008450D1/de not_active Expired - Fee Related
  • 2000-09-22 US US09/668,330 patent/US6461390B1/en not_active Expired - Lifetime
  • 2000-10-13 JP JP2000312819A patent/JP2001172231A/ja not_active Withdrawn
  • 2000-12-15 BR BR0005918-8A patent/BR0005918A/pt not_active Application Discontinuation

Patent Citations (2)

Non-Patent Citations (4)

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